AI prompt to run a small business insurance checkup

Commercial accounts involve more data, more forms and more markets. AI helps producers and account managers prepare submissions, renewals, certificates and coverage explanations faster, while specialized platforms handle quoting and market matching.

Below is a ready-to-copy prompt to run a small business insurance checkup, a detailed version that asks you clarifying questions first, and 2 specialized AI tools (Semsee and Bold Penguin) with instructions for this task. It also works in ChatGPT, Claude, Gemini or Copilot.

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The prompt

Create a 15-question small business insurance checkup that an agent can use in a conversation to spot common coverage gaps. Neutral, educational.

Detailed version (asks clarifying questions first)

Act as an experienced assistant to a licensed insurance agent. Before answering, ask me up to 3 clarifying questions (the type of business, the coverage line and who the output is for). Then complete this task, and finish with a short checklist of statements I should verify with my compliance team.

Task: Create a 15-question small business insurance checkup that an agent can use in a conversation to spot common coverage gaps. Neutral, educational.

What a good result looks like

A good checkup is a set of conversational questions about how the business really runs (what they do, where, with whom, what they own, who drives, what data they hold, what contracts require) that naturally reveal coverage gaps. It's educational, not a sales script.

Common mistakes and watch-outs

Don't diagnose a 'gap' as a fact before reviewing the policies. Some businesses need professional, cyber or workers' compensation coverage that depends on state law and operations, so keep it general. Note answers carefully; misstatements can affect applications later.

How to adapt the prompt

Add questions for the industry you're meeting (contractors, restaurants, offices). Afterward, comparative raters such as Semsee or Bold Penguin can help quote what you find.

EXAMPLE output (placeholder data, not a real client)

Small business insurance checkup (sample questions)

1. What does your business do day to day?
2. Do you work at customers' locations?
3. Do employees drive their own cars for work?
4. Do you store customer data or take card payments?
5. Do any contracts require certain insurance?
6. What equipment would be hard to replace?
7. Have you hired anyone recently?
8. Have you had any claims in the last few years?
...

How to use it

Copy the prompt. Copy the short prompt above, or the detailed version if you want the AI to ask clarifying questions first.
Add your details. Add the details for your situation (line of business, audience, tone). Keep it de-identified; never paste client personal information.
Run it in the right tool. Paste it into ChatGPT, Claude, Gemini or Copilot, or use Semsee and Bold Penguin as described below.
Review before you use it. Coverage depends on the actual policy form, state and carrier; tell clients to check their own policy. Check every fact, name and number yourself.
Take the next step. Next, see: Prepare a commercial submission.

Best AI tools for this task

Specialized tools first, ordered by fit for this task (never by payout), then any general AI assistant.

Semsee site ↗

Digital distribution platform connecting agents, partners, carriers and MGAs for commercial quoting.

How to use it

Quote any identified gaps across carriers in Semsee.

Bold Penguin site ↗

Commercial submission platform; states its DeX AI reads, prices and routes submissions to markets.

How to use it

Submit commercial risks through Bold Penguin.

Any AI assistant

ChatGPT Claude Google Gemini Microsoft Copilot

Paste the prompt above (short or detailed) into any of these.

Before you use it

Coverage depends on the actual policy form, state and carrier; tell clients to check their own policy.
Verify exposures, limits and forms against the actual application and policy.
Never paste client personal information (names, policy numbers, health or financial details) into AI tools your agency hasn't approved.
Review every AI output for accuracy and compliance before you use it.

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